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DOI: 10.1055/sos-SD-202-00407

Burns, N. Z.; Jacobsen, E. N.Science of Synthesis: Stereoselective Synthesis, (20112830.

Jacobsen has reported an acyl-Mannich reaction of isoquinolines with O-tert-butyldimethylsilyl O-isopropyl ketene acetal 7 catalyzed by thiourea 117 (Scheme 43).[‌65‌] The heterocycle is premixed with 2,2,2-trichloroethyl chloroformate and then treated with catalyst and nucleophile to yield enantioenriched 1-substituted dihydroisoquinoline 118. Several substituted isoquinolines are also reported as viable substrates for this transformation. The enamide in 118 can be readily reduced with triethylsilane and trifluoroacetic acid to give the tetrahydroisoquinoline.

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